title: Diastereoselective synthesis of alpha-tocopherol: a new concept for the formation of chromanols.
abstract: A diastereoselective synthesis of alpha-tocopherol 1 (93% de) was achieved via two key steps, (i) a highly diastereoselective Shi epoxidation of a trisubstituted alkene and (ii) an acid supported, "anti-Baldwin" epoxide ring opening under inversion of configuration leading to the 6-membered chromanol ring.
authors.affiliation: Department of Chemistry, University of Basel, Basel, Switzerland.
authors.forename: Julien
authors.initials: J
authors.lastname: Chapelat
authors.forename: Axel
authors.initials: A
authors.lastname: Buss
authors.forename: Antoinette
authors.initials: A
authors.lastname: Chougnet
authors.forename: Wolf-D
authors.initials: WD
authors.lastname: Woggon
mesh_terms: D002839:Chromans / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D024502:alpha-Tocopherol / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002839:Chromans; D004852:Epoxy Compounds; C029141:2,2,5,7,8-pentamethyl-1-hydroxychroman; D024502:alpha-Tocopherol